$103 Find Cheap Flights from Caribbean Islands to Washington, D.C.

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Washington, D.C. departing on 11/22. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Everything you should know

Cheapest round-trip
$155
Typical prices: $288-$550
Frontier
Thu 11/13Thu 12/4
SJU - IAD • 1 stop
Cheapest non-stop
$178
Typical prices: $273-$604
Frontier
Thu 11/6Sun 11/9
SJU - IAD • Non-stop
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Flight Deals
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Flight Deals

Cheap Flights from Caribbean Islands to Washington, D.C.

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Washington, D.C. that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean Islands to Washington, D.C.

Thu, Nov 13 - Thu, Dec 4
Frontier Logo
4:31 pm - 12:11 amSJU-IAD
8h 40m1 stop
Frontier Logo
10:08 am - 3:02 pmIAD-SJU
3h 54mnonstop
$155Frontier
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Wed, Oct 29 - Sun, Nov 2
Frontier Logo
9:00 am - 3:06 pmSJU-IAD
30h 06m2 stops
Frontier Logo
7:26 pm - 12:18 amIAD-SJU
3h 52mnonstop
$160Frontier
Find Deal
Thu, Nov 6 - Wed, Nov 12
JetBlue Logo
6:57 pm - 9:54 pmSJU-DCA
3h 57mnonstop
JetBlue Logo
8:00 am - 12:50 pmDCA-SJU
3h 50mnonstop
$216JetBlue
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Fri, Nov 14 - Sun, Nov 16
JetBlue Logo
6:51 pm - 9:48 pmSJU-DCA
3h 57mnonstop
JetBlue Logo
8:00 am - 12:50 pmDCA-SJU
3h 50mnonstop
$219JetBlue
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Wed, Nov 5 - Mon, Nov 10
American Airlines Logo
8:20 am - 10:15 pmSJU-DCA
14h 55m1 stop
American Airlines Logo
8:20 am - 8:48 pmDCA-SJU
11h 28m1 stop
$225American Airlines
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Fri, Nov 7 - Sat, Nov 15
American Airlines Logo
5:59 pm - 11:07 pmSJU-IAD
6h 08m1 stop
American Airlines Logo
8:09 pm - 1:13 pmIAD-SJU
16h 04m1 stop
$225American Airlines
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Thu, Nov 13 - Sun, Nov 16
United Airlines Logo
8:30 am - 11:35 amSJU-IAD
4h 05mnonstop
United Airlines Logo
5:32 pm - 10:22 pmIAD-SJU
3h 50mnonstop
$236United Airlines
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Thu, Nov 6 - Mon, Nov 10
Delta Logo
1:46 pm - 9:43 pmSJU-DCA
8h 57m1 stop
Delta Logo
6:07 am - 5:20 pmDCA-SJU
10h 13m1 stop
$245Delta
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Thu, Nov 20 - Sat, Dec 6
Delta Logo
3:20 pm - 11:04 pmSJU-DCA
8h 44m1 stop
Delta Logo
6:07 am - 5:20 pmDCA-SJU
10h 13m1 stop
$272Delta
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Fri, Feb 13 - Sat, Feb 21
United Airlines Logo
1:30 am - 11:59 pmPOS-DCA
23h 29m1 stop
United Airlines Logo
4:30 pm - 1:05 amDCA-POS
7h 35m1 stop
$405United Airlines
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Useful Info

Good to know

Low seasonSeptember
Cheapest flight$101
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from San Juan to Washington Dulles Airport

FAQs for booking flights from Caribbean Islands to Washington, D.C.

  • How does KAYAK find such low prices on flights from Caribbean Islands to Washington, D.C.?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Caribbean Islands to Washington, D.C..

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Washington, D.C.?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Washington, D.C. from Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Caribbean Islands to Washington, D.C.?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Washington, D.C. with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Washington, D.C.?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Washington, D.C. from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Caribbean Islands to Washington, D.C.

 
Need help choosing which airline to fly with from Caribbean Islands to Washington, D.C.? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 7984 reviews
7.9Comfort
7.3Food
8.2Boarding
8.5Crew
7.9Entertainment
Airline reviews

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

2.0 MediocreRyan, Oct 2025FCO - JFK
Read more Delta reviews

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

Crew was dismissive. Snacks and refills not offered. Poor business class experience. Bed not comfortable compared to Emirates or BA.

Flight was delayed for 5 hours because crew didn’t have enough time to rest - this seems like it could have been avoided with better scheduling. Food was not good.

IAD with the archaic people movers is just a place to be avoided.

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

This is the best united airlines flight that I took. The crew was very friendly and the food was tasty!

It is clear that someone knew, and competent, is in charge of food at United Airlines at least for the international flights. I was flying in coach, but the choices of the dinner were excellent. Tasty, and appropriate size. I had the beef, which was a little bit like a shepherds pie, and it was good. Nothing comparable has been served on a United flight in years. It will not be confused with three star food, but it is very good for airline food. Even better was the breakfast choice between a cinnamon roll and a breakfast sandwich. I chose the breakfast sandwich which was absolutely delicious and which I would happily order again at my local Starbucks or Panera. It is clear that someone knew indifferent is in charge of the food and it’s about time.

Had one staff that was not pleasant. Seems they are stressed with too many people to care for.

I would have liked an opportunity to move to a different seat ( even would have checked in my hand luggage)as I had health issues where I didn't have to clamber over the passenger next to me to for toilet use/ movement [ She was a highly unpleasant neighbor to sit next to]. In addition, I found that my European phone plan had run out of data and so I was not receiving emails from yourselves on airport wifi to be able to check in online and verifications difficult as did not accept the ticket number I had. I asked for an extra blanket but was told there was none. Then I saw other passengers receiving them. I couldn't eat the food and asked for snacks : Stewardess said " on the way" but they did not bring. The best bit was the check in process in Lisbon. Very efficient. However, I did not understand why we had to collect our bags at Washington then go through customs again. It was not explained. I also with my leg and health issue had approximately mile walk to the gate ( which then changed) . There appeared to be no moving walkways or help provided.

The attendant were friendly. I suggest you have a medical attendant on board every flight so that in case someone is sick , he/she will help them.

We had a very long diversion and our food voucher didn’t work because the restaurants were closed

A couple ladies from the crew were so rude and nasty. Thought they were mad at having to be there especially if you asked a question. This will make me think twice next time if I book a flight with you.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

The business class seats are dated and uncomfortable. The space is bare minimum and there is absolutely no privacy. For $4K, this is not what I expect.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

Initial flight was cancelled at the time of arrival to the airport, flight alternative requires switching from direct to flight with a layover, and the plane felt like it would split apart, it was so rattle-y.

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

Friendly crew. Poor food service maybe due to full flight. All in all, you get what you pay for.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

Vegas is such a quick flight that amenities aren’t the important part, in my opinion. Just get me there efficiently and safely, and that’s exactly what they did!

The flight was severely delayed due to the missing flight attendants.

Absolutely horrible. Usually pay $40-$50 to check luggage in. I tried to check my suitcase in and the price is raised to $70. That's ridiculously greedy c'mon. I had to leave my suitcase with all my clothes and hygiene products and repurchase once i landed in Atlanta. You guys make it really stressful to travel. Don't even want to travel anymore.

They cancelled the flight 3 hours prior departure. Had to spend $400 for a ne way flight with Delta Airlines! Spirit Airlines are not serios!

My luggage didn’t arrive at LAX, so that wasn’t a good experience.

Terrible seat, no in flight entertainment. No complimentary food or drinks. Seats really hurt my back after flying spirit for the day.

Plastic seat really hurt my back. Cannot even recline on the flight. Very hard to sleep on the plane due to terrible seats . Food and drinks were expensive and not very good. There were like 2 open exit rows behind me. My isle was full so I asked flight attendants if I could sit there. They told me it was a safety issue??? I think it more unsafe to have no one sitting there. In case of emergency, you’d want someone there to help.

Over SOLD flight. It does not matter that you were able to check in 24 Hours before and confirm your flight. At the airport, the company SPIRIT rep wanted to remove people who pay for lower fares.

The delays and the lack of communication and organization within the airport itself for Staffing this flight and coordinating the paper log necessary to depart was ridiculous and deplorable

It was a no show, so we got put in hotels for a nite. The A320 plane was very modern and flite and crew (if a pilot shows up were fine). Price was very good.

Traveling to a place near Washington, D.C.?

Book flights to Washington, D.C. if you plan to visit one of these locations
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Everything you need to know for your flight to Washington, D.C.

Cabin class types available on flights to Caribbean Islands

Cabin classes available on flights to Washington, D.C.. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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